As an investor, founder, CEO and business book author, I write about startups, design, how to build a good business, and I like to muse about culture in any form.

My parking ticket payment saga

Great meeting last month with a crazily dynamic and accomplished startup attorney, Sarah Reed.  She helped me discover Koo Koo cafe in Brookline.  Sat outside, dodging raindrops and sun at the same time, and parked the Rambler Ambassador right within sight.  But somehow missed the meter maid and got saddled with a parking ticket.

Just now scanned the ticket for payment options. Cool.  I can pay at  I hit the site and spend two or three minutes scanning every homepage menu item.  Nothing listed that even comes close to a ticket paying option.  A couple fruitless clicks and I was just starting to look for a search box.   (If you want to follow along in my journey, go right now to the site and search for a way to pay tickets.  Don’t read ahead.)  Just about to give up, I notice an animated advertisement in the header “Pay Your Tickets Online”.  It looked so much like a real, friendly, consumer-directed ad that I did what I usually do.  I ignored it.  Without even knowing I was ignoring it. Ouch.

As a consumer, I want ad-based sites to succeed.  They’re the main reason I get good stuff for free.  As an entrepreneur I have the same wish…that ad models continue to provide a platform for cool development work.

In that vein, I met with a startup founder today.  He has a good idea that could actually justify a high CPM ad revenue model.  But here’s the thing that is at the heart (and Achilles heel) of those models.  When we are all too busy “doing” stuff online (great post by David Beisel on this), the ads slip right by us all.

Reams of pixels (OK, piles of pixels) have been spilled on the difficulty of assembling enough eyeballs to make real ad money. I’ve been on the inside of just such an ocular assembly effort, and for the same reason that you pick chocolate when you’ve OD’d on vanilla, I steer clear of throwing myself at that kind of work these days.

My parking ticket journey just confirmed the choice.

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